Formation of azomethine ylids by thermolysis of oxazolidines. Study of the reaction in solution and in the gaseous phase
Thermolysis of oxazolidines leads to azomethine ylids via cycloreversion.In the liquid phase, these intermediates then give 1-3 dipolar cycloaddition; in the gaseous phase, they lead to aziridines.With an alkyl group in position 2, we observed also the formation of enamines.The effect of substituents on both the cycloreversion reaction and the evolution of azomethine ylids was studied.The mechanism of the process tautomerism aziridine -> azomethine ylid -> enamine is discussed.Keywords - azomethine ylids / oxazolidines / cycloreversion / aziridines / enamines / tautomerism
Bureau, R.,Mortier, J.,Joucla, M.
p. 584 - 596
(2007/10/02)
Flash vacuum thermolysis of 2-isopropyl oxazolidines. Mechanism of the tautomerism between azomethine ylid, aziridine and enamine
Depending on the nature of the substitution of 2-isopropyl oxazolidines and the Flash Vacuum Thermolysis conditions, aziridines and/or enamines are recovered through the azomethine ylid formed in situ Studies with deuterium labelled molecules give arguments for a concerted process in the gas phase.
Bureau, Ronan,Joucla, Marc
p. 6017 - 6020
(2007/10/02)
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